Set Sail for a By-Gone Era

Step back into history when you join the crew of the Yorktown Schooner Alliance or Schooner Serenity.  Lend a hand at setting sail, take the helm and steer the ship, or look for dolphins and osprey as you glide along the shores of the York River.   You will relive sailings Golden Age as you cruise past the Victory Monument and Battlefield where our country won its independence.

For those who love history, yearn for romance, or have dreamed of a true sailing adventure, setting sail on the historic waters of Yorktown, VA is a magical experience. Let yourself fall into the rich surrounding history and the majestic ship you’re aboard while amongst family and friends – a fresh breeze pulling it all together. It’s our passion at Yorktown Sailing Charters to introduce you to the beauty of the waters we’ve been sailing for over 30 years, give you lifelong memories and keep you coming back for more.

Whether you’re looking for things to do in Williamsburg VA or searching among the best sailing charters on the Chesapeake Bay, your journey stops with us. Our impressive vessel,  the Alliance, is a historic beauty sailing in Yorktown for the summer and exploring the Caribbean in the winter.

Yorktown Cruises & Sailing Specials

Special events are welcome as we are pleased to offer private sailing charters for weddings, corporate cruises, our own exciting pirate cruises and more. Among the popular pirate cruises you will watch as the kids raise the sails, learn sailors skills and truly experience what it was like years ago aboard a schooner! Food and beverages are conveniently available for purchase aboard the ship completing your day out on the water.

For the ultimate enjoyment of a day of sailing come join Yorktown Sailing Charters. After boarding the Alliance or the Serenity you’ll understand why so many satisfied customers have raved about our sailing cruises for years! We look forward to introducing you to the history, romance and beauty found in and around our boats.

Yorktown Cruise Ships & Sailing Charters Events

Thank you for checking out our website. Continue browsing around for more information on our Chesapeake Bay and Yorktown, VA sailing and boat tours. In addition to these sailing charters, you will also find information on our Caribbean Islands winter week charters. Let us show you the pleasures of a Caribbean sailing cruise. If you have questions about any of our tours or how you can book a tour, give us a call today at 888-316-6422 or send an email. We look forward to hearing from you and taking you on your next sailing tour!